For One Cleveland Journalist, Flipping Houses Is an Obsession

You’re supposed to stay detached when flipping houses, but if a place has even a hint of character — original woodwork, pocket doors — I’m already gone. Before I’ve checked the foundation or roofline, I’m imagining where the chandelier will hang, where the sideboard will go.

One Sunday morning, I found a house in Cleveland’s Hough neighborhood. I spotted the listing on my phone while driving across town and pulled into the driveway between errands and dropping my daughter off at youth group.

Built in 1910 and surrounded by vacant lots and newer homes from the 1990s and 2000s, it was one of the few original houses left on the street. Others had disappeared — lost to redlining, the housing collapse of 2008-2009 or the city’s demolition policies. Somehow, amid the empty lots and vinyl-sided colonials, this one had survived.

From the outside, I could see wood shake siding, painted forest green and badly peeling, and two circular turrets — one on the side, one in front. I used my realtor’s license to set up a showing on my phone. Inside, the house was in rough shape, but it hadn’t been stripped of its character. There were four ornate fireplaces — two downstairs, two upstairs — and a wood-beamed dining room ceiling buried under paint. The bedrooms were large, with real closets. I peeled back a corner of the carpet: hardwood floors.

Oh, man — I was smitten.

I have a problem. I’m addicted to house hunting — not watching HGTV, but fantasizing about renovating homes in Cleveland’s historic neighborhoods and selling them for a profit. My wife should probably be relieved my midlife crisis involves real estate listings instead of strippers and cocaine, though she might say otherwise.

I don’t have the capital to be a real flipper; my renovation skills top out at painting and peel-and-stick tile. Still, that doesn’t stop me.

“Take a look at this house,” I texted my friend Dave, who owns a real estate company. It was listed at $140,000, with a new roof and driveway, but it needed everything else. I told him about its location near the Cleveland Clinic and nearby development. I figured it would cost at least $200,000 to renovate. Would it sell for $400,000 or more?

“I’ll take a look,” he wrote. “Sounds risky.”

He was right. This wasn’t my first attempt. I owned a couple of rentals, and my wife and I lived in a house we’d bought out of foreclosure and renovated. But lately, this side hustle had become an obsession — a distraction from writing and my day job. I convinced myself that if I could just find the right house, I could make a living flipping homes.

My parents planted the seed. When I was a kid, they dragged me along to mow lawns at the duplexes they owned in Cleveland Heights — a suburb built for white families fleeing neighborhoods like Hough. Even now, my family trades contractor recommendations the same way that others swap recipes.

My wife and I live in a West Side neighborhood near Downtown, on a street of people like us — neighbors committed to fixing up old houses and raising kids in the city. On weekends, there are firepits, porch happy hours, long conversations while walking the dog. Aside from the occasional police chase or car theft, it feels like a small, hard-won urban bliss.

That spring, I toured dilapidated houses across Cleveland. I used my phone’s flashlight to navigate moldy basements, sagging drop ceilings, and listings that stretched the definition of “bedroom.” It’s one thing to answer a multiple-choice question about “functional obsolescence” on a licensing exam; it’s another to stand in a house where the only bathroom is a stained afterthought off the kitchen.

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Why was I doing this when I should have been working on my book? Late at night, sitting in my son’s darkened room while he drifted to sleep, I’d scroll through listings, tapping red dots on the map, chasing the next possibility — a kind of productive procrastination to avoid the harder work of writing. I’d leave his room bleary-eyed, telling myself this was a mistake even as I imagined the next project. It was fueled by a familiar set of doubts: that I’m not good enough, that I’m a fraud.

Still, I couldn’t shake the restlessness. Maybe it was turning 48. Maybe it was the pandemic, or the cost of raising kids, or the quiet panic of wondering how we’d pay for college Whatever the cause, it led me to that house in Hough — a place that would need to be taken down to the studs and rebuilt.

My crush faded within weeks. The cost of renovating it — or any house like it — was beyond my reach. The seller had bought it at a sheriff’s sale for $22,000 and was asking $140,000, and the market was cooling as interest rates climbed past 6%. Reluctantly, I let it go.

Later that year, my wife and I bought the house next door. An investor had planned to flip it, but instead of allowing another low-quality renovation on our street, we negotiated to buy it and do it right. With a historic rehab loan and money borrowed from my parents, we’re turning it into an Airbnb — something that, with luck, will become a real asset for our family. It’s probably the last house I’ll buy for a while; it will take all our resources to pull off.

I doubt the fantasy will ever fully fade. It’s impractical, but it has a hold on me. These days, I’m a little less distracted. Work has steadied. I’ve started a new manuscript. But when I hit a wall — or late at night, when worry creeps in about camp tuition or orthodontist bills — I still reach for my phone. I open that little red house app and click on a listing: a bungalow with peeling paint, a deep front porch, leaded-glass windows.

Before I even see the inside, I’m already choosing paint colors.

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